NPASS Compound

Natural Product: NPC5883

Natural Product ID	NPC5883
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Neritaloside
IUPAC Name	[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms	Neritaloside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510771
PubChem CID	44566654
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 90 95 0 0 0 0 0 0 0 0999 V2000 -7.8181 2.1574 -1.9521 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7052 1.1373 -1.8643 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3309 -0.2150 -1.6225 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4087 -0.5103 -0.1201 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0455 -0.4045 0.5291 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1397 0.3342 -0.4304 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7970 1.4729 -0.8601 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9612 0.6319 0.2293 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8563 -0.0128 -0.3243 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9379 1.0149 -0.8813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9737 1.5049 0.1470 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1350 0.4387 0.7769 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0200 0.8285 2.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7654 -0.9271 0.7299 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2371 -1.7894 -0.4069 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2513 -2.0056 -0.2752 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9197 -0.8707 0.4703 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1979 0.3911 0.0660 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0333 1.6193 0.2464 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1247 1.3362 1.2483 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1261 0.3140 0.7771 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8890 -0.1823 1.9836 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0282 0.7967 -0.3095 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2734 1.4409 0.1055 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5258 1.1723 -0.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4539 2.0908 0.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7181 2.1214 0.3781 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6858 2.9603 1.1932 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3494 2.5891 1.0456 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1778 -0.3883 -1.2123 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6697 -0.7654 -1.3352 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3697 -0.8549 0.1650 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9371 -2.0487 0.6026 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8312 -1.4852 -0.6143 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8317 -2.2211 -1.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2296 -1.9184 -2.3372 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4641 -3.3655 -0.4696 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2638 -0.8822 0.7421 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5434 -1.6817 0.8133 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2535 0.4599 0.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3552 -0.1620 0.9554 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6440 -0.1715 -2.0825 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0967 2.3389 -3.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5835 3.0843 -1.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7592 1.7504 -1.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1715 1.0855 -2.8218 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7994 -1.0216 -2.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8076 -1.5211 0.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0811 0.1726 1.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9102 -0.3655 -1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2521 -0.6194 -1.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5664 1.9072 -1.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4502 0.7113 -1.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3430 2.2976 -0.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5730 2.0779 0.9141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4329 1.8279 2.3864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4829 0.0301 2.8449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0454 0.8908 2.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4492 -1.4606 1.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5617 -1.4687 -1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7060 -2.8030 -0.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6432 -1.9942 -1.3339 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5114 -2.9963 0.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8025 -1.0962 1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9691 0.2938 -1.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0419 -0.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4071 2.4309 0.7017 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6133 0.8665 2.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5830 2.2496 1.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5839 -1.2138 2.2711 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6298 0.4606 2.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9863 -0.0977 1.8477 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4001 1.5325 -0.9209 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8700 0.3897 -0.8555 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8815 2.3308 2.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7996 3.4515 0.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5713 -0.1403 -2.1896 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1978 0.0827 -1.8243 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5958 -1.7357 -1.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2959 -2.6426 1.0446 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3587 -3.2197 0.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9870 -4.3313 -0.7051 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5676 -3.4207 -0.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6349 -1.9146 0.5931 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5925 -0.5576 1.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9621 -1.6004 1.5954 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9417 -0.7504 0.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0911 -0.8208 1.8055 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0738 0.5957 1.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0594 -1.0589 -2.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 23 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 30 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 14 38 1 0 5 39 1 0 4 40 1 0 40 41 1 0 3 42 1 0 7 2 1 0 38 9 1 0 18 12 1 0 32 21 1 0 32 17 1 0 29 24 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 6 4 48 1 6 5 49 1 1 6 50 1 6 9 51 1 6 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 13 56 1 0 13 57 1 0 13 58 1 0 14 59 1 1 15 60 1 0 15 61 1 0 16 62 1 0 16 63 1 0 17 64 1 1 18 65 1 6 19 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 22 70 1 0 22 71 1 0 22 72 1 0 23 73 1 6 25 74 1 0 29 75 1 0 29 76 1 0 30 77 1 6 31 78 1 0 31 79 1 0 33 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 38 84 1 0 38 85 1 0 39 86 1 0 41 87 1 0 41 88 1 0 41 89 1 0 42 90 1 0 M END

Standard InCHIKey	UZQOZJNEDXAJEZ-VZJXLKLWSA-N
Standard InCHI	InChI=1S/C32H48O10/c1-16-26(35)28(38-5)27(36)29(40-16)42-20-8-10-30(3)19(13-20)6-7-22-21(30)9-11-31(4)25(18-12-24(34)39-15-18)23(41-17(2)33)14-32(22,31)37/h12,16,19-23,25-29,35-37H,6-11,13-15H2,1-5H3/t16-,19-,20+,21+,22-,23+,25+,26+,27-,28+,29+,30+,31-,32+/m1/s1
SMILES	C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C4=CC(=O)OC4)[C@H](C[C@]32O)OC(=O)C)C1)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.32	Volume:	590.682 ? Van der Waals volume.
Dense:	1.003	LogP:	1.832 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.34 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.916 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	33.0
TPSA:	140.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.322	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.289	Fsp³:	0.875
MCE-18:	113.433 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.792	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.026 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.132	Promiscuous compounds:	0.708

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.504	MDCK Permeability:	-5.111
Pgp-inhibitor:	0.97	Pgp-substrate:	0.975
PAMPA:	0.966 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.65	30% Bioavailability (F30%):	0.884
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.802
Plasma Protein Binding (PPB):	64.719%	Volume Distribution (VD):	-0.409
Fu:	33.261% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.769	BCRP inhibitor:	0.031
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.046	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.802	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.667	CYP3A4-substrate:	0.653
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.01
HLM stability:	0.081 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.625

Half-life (T1/2):

3.445

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.358
Human Hepatotoxicity (H-HT):	0.359	Drug-induced Liver Injury (DILI):	0.819
AMES Toxicity:	0.789	Rat Oral Acute Toxicity:	0.668
Maximum Recommended Daily Dose:	0.936	Skin Sensitization:	1.0
Carcinogencity:	0.516	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.638
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.817
Hematotoxicity:	0.832	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	0.969	RPMI-8226 Immunitoxicity:	0.538
A549 Cytotoxicity:	0.083	Hek293 Cytotoxicity:	0.492
BCF:	0.496 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.34 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.05 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.191 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/ncomms4886]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37726667]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39382805]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	60

Activity Type	# Activity
Cell line	60

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	98.63	nM	PubChem BioAssay data set
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	15.21	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	26.98	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	17.74	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	18.84	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	56.62	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	148.94	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	17.58	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	24.83	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	40.55	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	16.03	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	281.19	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	140.6	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	22.91	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	21.13	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	25.29	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	79.8	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	48.64	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	72.28	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	91.41	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	143.88	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	198.15	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	53.33	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	110.66	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	16.44	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	14.22	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	156.68	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	90.36	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	170.22	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	40.93	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	60.12	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	70.79	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	33.11	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	128.82	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	10.38	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	230.14	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	111.94	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	21.88	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	97.27	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	24.04	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	15.56	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	159.96	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	25.59	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	161.81	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	80.72	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	16.52	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	123.59	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	20.84	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	37.15	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	46.13	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	20.23	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	17.62	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	28.97	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	172.58	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	46.13	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	291.07	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	156.31	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	16.37	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC5883 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	15269
0.1-0.2	29649
0.2-0.3	4572
0.3-0.4	192
0.4-0.5	107
0.5-0.6	38
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7857	Intermediate Similarity	NPC103534
0.7857	Intermediate Similarity	NPC44899
0.7857	Intermediate Similarity	NPC488935
0.7857	Intermediate Similarity	NPC304260
0.7857	Intermediate Similarity	NPC488936
0.7857	Intermediate Similarity	NPC29639
0.7778	Intermediate Similarity	NPC479356
0.7778	Intermediate Similarity	NPC479355
0.7683	Intermediate Similarity	NPC199428
0.7683	Intermediate Similarity	NPC109448
0.7683	Intermediate Similarity	NPC310341
0.7204	Intermediate Similarity	NPC488943
0.7204	Intermediate Similarity	NPC488942
0.6768	Remote Similarity	NPC488945
0.6768	Remote Similarity	NPC488946
0.6667	Remote Similarity	NPC55532
0.6667	Remote Similarity	NPC488938
0.6667	Remote Similarity	NPC488937
0.6591	Remote Similarity	NPC250556
0.6517	Remote Similarity	NPC305574
0.6512	Remote Similarity	NPC479351
0.6512	Remote Similarity	NPC479352
0.6392	Remote Similarity	NPC475219
0.6373	Remote Similarity	NPC488947
0.6341	Remote Similarity	NPC119855
0.6154	Remote Similarity	NPC93883
0.6	Remote Similarity	NPC99080
0.5955	Remote Similarity	NPC99620
0.5934	Remote Similarity	NPC84949
0.5934	Remote Similarity	NPC480562
0.5934	Remote Similarity	NPC74945
0.5934	Remote Similarity	NPC31354
0.5934	Remote Similarity	NPC69576
0.5714	Remote Similarity	NPC486129
0.5652	Remote Similarity	NPC486126
0.5604	Remote Similarity	NPC471633
0.5556	Remote Similarity	NPC231518
0.5556	Remote Similarity	NPC488944
0.55	Remote Similarity	NPC486143
0.55	Remote Similarity	NPC486142
0.55	Remote Similarity	NPC486149
0.5484	Remote Similarity	NPC5311
0.5417	Remote Similarity	NPC193893
0.5412	Remote Similarity	NPC471770
0.5361	Remote Similarity	NPC72260
0.5312	Remote Similarity	NPC484202
0.5306	Remote Similarity	NPC157817
0.53	Remote Similarity	NPC486151
0.5253	Remote Similarity	NPC30483
0.5253	Remote Similarity	NPC470897
0.5243	Remote Similarity	NPC486146
0.5238	Remote Similarity	NPC479360
0.5238	Remote Similarity	NPC479359
0.5189	Remote Similarity	NPC486144
0.5189	Remote Similarity	NPC486145
0.5189	Remote Similarity	NPC486147
0.5189	Remote Similarity	NPC486148
0.5158	Remote Similarity	NPC469750
0.5104	Remote Similarity	NPC76572
0.5104	Remote Similarity	NPC193382
0.505	Remote Similarity	NPC236973
0.505	Remote Similarity	NPC142756
0.505	Remote Similarity	NPC292467
0.5046	Remote Similarity	NPC486134
0.5046	Remote Similarity	NPC486141

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC5883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6151
0.1-0.2	2871
0.2-0.3	112
0.3-0.4	6
0.4-0.5	2
0.5-0.6	4
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6591	Remote Similarity	NPD7507	Pre-clinical
0.5556	Remote Similarity	NPD8033	Approved
0.55	Remote Similarity	NPD8377	Phase 4
0.5361	Remote Similarity	NPD8294	Phase 4
0.5052	Remote Similarity	NPD8335	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data